US20210251267A1 - Ligustrosidic acid and derivatives thereof for sweetness enhancement - Google Patents

Ligustrosidic acid and derivatives thereof for sweetness enhancement Download PDF

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Publication number
US20210251267A1
US20210251267A1 US17/259,307 US201917259307A US2021251267A1 US 20210251267 A1 US20210251267 A1 US 20210251267A1 US 201917259307 A US201917259307 A US 201917259307A US 2021251267 A1 US2021251267 A1 US 2021251267A1
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Prior art keywords
sweetness
rebaudioside
ppm
derivative
acid
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US17/259,307
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Ajay Pratap Singh
Hassan Mustaq Ubaideen
Jung-a Kim
Xiao-Qing Tang
Hsi-Wen Chin
Michelle Eve Huber
Xiaodong Li
Thumpalasseril V. John
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International Flavors and Fragrances Inc
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International Flavors and Fragrances Inc
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Priority to US17/259,307 priority Critical patent/US20210251267A1/en
Assigned to INTERNATIONAL FLAVORS & FRAGRANCES INC. reassignment INTERNATIONAL FLAVORS & FRAGRANCES INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHIN, HSI-WEN, HUBER, Michelle Eve, JOHN, THUMPALASSERIL V., KIM, JUNG-A, LI, XIAODONG, SINGH, AJAY PRATAP, TANG, XIAO-QING, UBAIDEEN, Hassan Mustaq
Publication of US20210251267A1 publication Critical patent/US20210251267A1/en
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A23L27/12—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1307—Milk products or derivatives; Fruit or vegetable juices; Sugars, sugar alcohols, sweeteners; Oligosaccharides; Organic acids or salts thereof or acidifying agents; Flavours, dyes or pigments; Inert or aerosol gases; Carbonation methods
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A23L27/12—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils
    • A23L27/13—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils from citrus fruits
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • Reducing sugar content in food and beverages has become a necessity in the food industry.
  • Food and beverage manufacturers generally use non-caloric, high-intensity sweetness modifiers, such as rebaudioside A (Reb A), aspartame, saccharin, glycosylated steviol glycosides, etc., to partially or completely replace sugar.
  • these sweetness modifiers may exhibit undesirable taste attributes such as delayed onset of sweetness, bitter and astringent aftertaste, and lack of body and mouthfeel. Consequently, sweetness enhancers have become valuable tools, which reduce the use of sugar and/or sweetness modifiers, in achieving the desired sweetness intensity and mouthfeel with reduced off-taste.
  • Sweetness enhancers have been described in the prior art.
  • WO 2013/143822 teaches the use of adenosine as sweetness enhancer for certain sugars
  • EP 2606747 describes the use of deoxycholic acid or a derivative thereof for enhancing the sweetness of consumables
  • WO 2013/077668 describes the sweetness enhancing effect of a glycan or glycopeptide derived from soy sauce
  • WO 2012/107203 teaches the use of nobiletin or a derivative or a hydrate thereof as a sweetener or sweetness enhancer
  • WO 2009/023975 describes the use of iso-mogroside V as a sweetener and sweetness enhancer
  • US 2008/0242740 teaches aroma compositions of alkamides with hesperetin and/or 4-hydroxydihydrochalcones for enhancing sweet sensory impressions
  • WO 2007/014879 and WO 2007/107596 respectively teach the use of hesperetin and 4-hydroxydihydrochalcone
  • This invention provides a method of enhancing the sweetness of a sweetness modifier by adding an olfactory effective amount of ligustrosidic acid or a derivative thereof.
  • Ligustrosidic acid and its derivative, 2′-hydroxy ligustrosidic acid are represented by formulas set forth below:
  • the present invention is directed to a method of enhancing the sweetness of a sweetness modifier comprising the step of adding an olfactory effective amount of ligustrosidic acid or a derivative thereof.
  • the present invention is directed to a method enhancing the sweetness of a sweetness modifier comprising the step of adding an olfactory effective amount of Carica papaya leave extract.
  • the present invention is directed to a composition
  • a composition comprising a sweetness modifier and an olfactory effective amount of ligustrosidic acid or a derivative thereof.
  • the present invention is directed to a composition
  • a composition comprising a sweetness modifier and an olfactory effective amount of Carica papaya leave extract.
  • the present invention is directed to a consumable comprising a sweetness modifier and an olfactory effective amount of ligustrosidic acid or a derivative thereof.
  • the present invention is directed to a consumable comprising a sweetness modifier and an olfactory effective amount of Carica papaya leave extract.
  • Ligustrosidic acid [3-(carboxymethylene)-2-( ⁇ -D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)]-2H-pyran-4-acetic acid- ⁇ -[2-(4-hydroxyphenyl)ethyl]ester, and its derivative, 2′-hydroxy ligustrosidic acid, are naturally constituents in Ligustrum lucidum Ait and Ligustrum japonicum.
  • Ligustrum lucidum Ait has been used as a traditional Chinese medicine over thousands of years in invigorating liver and kidney (Hu et al., Oncology Reports (2014), 32(3):1037-1042).
  • Other species such as Ligustrum liukiuense, Ligustrum lucidum, Ligustrum morrisonense, Ligustrum pricei , and Ligustrum sinense have been widely used as tea or herbal medicine in Europe, China and Japan (Wu et al. Food Chemistry (2011), 127(2), 564-571).
  • the extract of Ligustrum sinense was also evaluated in a combined treatment of Pseudomonas aeruginosa PA01 biofilm formation with gentamicin sulphate (Yang et al.
  • ligustrosidic acid and 2′-hydroxy ligustrosidic acid have been for the first time identified in genus Carica . Further, ligustrosidic acid and 2′-hydroxy ligustrosidic acid have also been found to possess an unexpected and advantageous use in food. In particular, ligustrosidic acid, 2′-hydroxy ligustrosidic acid, a salt thereof or a mixture thereof has been found to enhance the sweetness of sweetness modifiers without undesirable off-notes.
  • the present invention provides a method of using ligustrosidic acid, 2′-hydroxy ligustrosidic acid, a salt thereof or a mixture thereof to enhance the sweetness of a sweetness modifier and decrease the amount of a sweetness modifier used in a consumable.
  • ligustrosidic acid or a derivative thereof is understood to mean ligustrosidic acid, 2′-hydroxy ligustrosidic acid, a salt thereof or a mixture thereof.
  • ligustrosidic acid and 2′-hydroxy ligustrosidic acid are available commercially and can also be an isolated and purified form a botanical extract, for example, genus Ligustrum such as Ligustrum amamianum, Ligustrum amurense, Ligustrum angustum, Ligustrumantenum, Ligustrum chenaultii, Ligustrum compactum, Ligustrum confusum, Ligustrum delavayanum, Ligustrum expansum, Ligustrum gracile, Ligustrum henryi, Ligustrum ibota, Ligustrum indicum, Ligustrum japonicum, Ligustrum leucanthum, Ligustrum lianum, Ligustrum liukiuense, Ligustrum longitubum, Ligustrum lucidum, Ligustrum massalongianum, Ligustrum micranthum, Ligustrum microcarpum, Ligustrum morrisonense, Ligustrum obovatilimbum, Ligustrum obtusi
  • the extract is enriched for ligustrosidic acid and 2′-hydroxy ligustrosidic acid to achieve a content of about 0.01% and greater, respectively.
  • the botanical extract contains each of ligustrosidic acid and 2′-hydroxy ligustrosidic acid from about 0.05% to about 95%, from about 0.1% to about 50% or from about 0.2% to about 10%. Unless otherwise specified, percentages (% s) are by weight.
  • a natural sweetener includes, for example, but not limited to, sucrose, fructose, glucose, high fructose corn syrup, Stevia rebaudiana compositions including pure components of Reb A, stevioside, and rebaudioside D (Reb D), xylose, arabinose, or rhamnose, as well as sugar alcohols such as erythritol, xylitol, mannitol, sorbitol, inositol and a combination thereof.
  • An artificial sweetener includes, for example, but not limited to, aspartame, sucralose, neotame, acesulfame potassium, saccharin and a combination thereof.
  • a flavoring is a preparation that provides a consumable with a particular taste and/or smell.
  • a flavoring with modifying properties is a subset of the flavoring. It is added to the consumable to reduce off-notes and/or improve overall profile.
  • the flavorings with modifying properties of the present invention include, for example, but not limited to, a Stevia composition including stevioside, steviolbioside Reb A, rebaudioside B (Reb B), rebaudioside C (Reb C), Reb D, rebaudioside E (Reb E), rebaudioside F (Reb F), dulcoside A, dulcoside B, rubusoside, alpha-glucosyl Stevia , fructosyl Stevia , galactosyl Stevia , beta-glucosyl Stevia , siamenoside, mogrosidc IV, mogroside V, Luo Han Guo, monatin, glycyrrhizic acid, thaumatin
  • the glycosylated derivatives can be prepared via transglycosylation reactions with, for example, but not limited to, glucose, fructose, galactose, rhamnose, ribose, mannose, arabinose, fucose, maltose, lactose, sucrose, rutinose, sorbose, xylulose, ribulose, rhammulose and xylose.
  • the flavorings with modifying properties of the present invention include Reb A, Reb C, rubusoside, Reb D, mogroside V, Luo Han Guo, monatin acid, a salt thereof, a glycosylated derivative thereof and a combination thereof.
  • the flavorings with modifying properties of the present invention exhibit weak intrinsic sweetness.
  • Some other flavorings of the present invention include, for example, but not limited to, curculin, monellin, mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobtain, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, cyclocarioside I and a combination thereof.
  • a sweetness modifier refers to a sweetener including a natural sweetener and an artificial sweetener or a flavoring with modifying properties set forth in the above.
  • sweetness or “sweetness intensity” is understood to mean the relative strength of sweet sensation as observed or experienced by an individual, e.g., a human, or a degree or amount of sweetness detected by a taster, for example on the scale from 0 (none) to 8 (very strong) used in sensory evaluations according to the procedure described in American Society for Testing Materials, Special Technical Publication-434: “Manual on Sensory Testing Methods,” ASTM International, West Conshohocken, Pa. (1996).
  • olfactory effective amount is understood to mean the amount of ligustrosidic acid or a derivative thereof used in a combination with a sweetness modifier, wherein ligustrosidic acid or a derivative thereof enhances the sweetness of the sweetness modifier. Its olfactory effective amount may vary depending on many factors including other ingredients, their relative amounts and the olfactory effect that is desired. Any amount of ligustrosidic acid or a derivative thereof that provides the desired degree of sweetness enhancement without exhibiting off-taste can be used.
  • the olfactory effective amount ranges from about 1 ppb to about 1000 ppm by weight, preferably from about 5 ppb to about 100 ppm by weight and more preferably from about 10 ppb to about 10 ppm by weight.
  • the olfactory effective amount ranges from about 100 ppb to about 1000 ppm by weight, preferably from about 1 to about 500 ppm by weight and more preferably from about 5 to about 200 ppm.
  • a consumable includes, for example, a food product (e.g., a beverage), a sweetener such as a natural sweetener or an artificial sweetener, a pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition and a cosmetic product.
  • a food product e.g., a beverage
  • a sweetener such as a natural sweetener or an artificial sweetener
  • a pharmaceutical composition e.g., a dietary supplement, a nutraceutical, a dental hygienic composition
  • the consumable may further contain a flavoring.
  • a consumable is a food product including, for example, but not limited to, fruits, vegetables, juices, meat products such as ham, bacon and sausage, egg products, fruit concentrates, gelatins and gelatin-like products such as jams, jellies, preserves and the like, milk products such as yogurt, ice cream, sour cream and sherbet, icings, syrups including molasses, corn, wheat, rye, soybean, oat, rice and barley products, nut meats and nut products, cakes, cookies, confectionaries such as candies, gums, fruit flavored drops, and chocolates, chewing gums, mints, creams, pies and breads.
  • the food product is a beverage including, for example, but not limited to, coffee, tea, carbonated soft drinks, such as COKE and PEPSI, non-carbonated soft drinks and other fruit drinks, sports drinks such as GATORADE and alcoholic beverages such as beers, wines and liquors.
  • a consumable also includes prepared packaged products, such as granulated flavor mixes, which upon reconstitution with water provide non-carbonated drinks, instant pudding mixes, instant coffee and tea, coffee whiteners, malted milk mixes, pet foods, livestock feed, tobacco, and materials for baking applications, such as powdered baking mixes for the preparation of breads, cookies, cakes, pancakes, donuts and the like.
  • a consumable also includes diet or low-calorie food and beverages containing little or no sucrose.
  • a preferred consumable includes carbonated beverages.
  • Consumables further include condiments such as herbs, spices and seasonings, flavor enhancers (e.g., monosodium glutamate), dietetic sweeteners and liquid sweeteners.
  • a consumable is a pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition or a cosmetic product.
  • Preferred compositions are pharmaceutical compositions containing ligustrosidic acid or a derivative thereof, one or more pharmaceutically acceptable excipients, and one or more active agents that exert a biological effect other than sweetness enhancement.
  • active agents include pharmaceutical and biological agents that have an activity other than taste enhancement.
  • Such active agents are well known in the art (See, e.g., The Physician's Desk Reference).
  • Such compositions can be prepared according to procedures known in the art, for example, as described in Remington's Pharmaceutical Sciences, Mack Publishing Co., Easton, Pa.
  • such an active agent includes a bronchodilator, an anorexiant, an antihistamine, a nutritional supplement, a laxative, an analgesic, an anesthetic, an antacid, a H2-receptor antagonist, an anticholinergic, an antidiarrheal, a demulcent, an antitussive, an antinauseant, an antimicrobial, an antibacterial, an antifungal, an antiviral, an expectorant, an anti-inflammatory agent, an antipyretic and a mixture thereof.
  • the active agent is selected from the group consisting of an antipyretic and analgesic, e.g., ibuprofen, acetaminophen or aspirin, a laxative, e.g., phenolphthalein dioctyl sodium sulfosuccinate, an appetite depressant, e.g., an amphetamine, phenylpropanolamine, phenylpropanolamine hydrochloride, or caffeine, an antacid, e.g., calcium carbonate, an antiasthmatic, e.g., theophylline, an antidiarrheal, e.g., diphenoxylate hydrochloride, an agent against flatulence, e.g., simethecon, a migraine agent, e.g., ergotamine tartrate, a psychopharmacological agent, e.g., haloperidol, a spasmolytic or sedative,
  • dietary supplements or nutraceuticals include, for example, but are not limited to, an enteral nutrition product for treatment of nutritional deficit, trauma, surgery, Crohn's disease, renal disease, hypertension, obesity and the like, to promote athletic performance, muscle enhancement or general well-being or inborn errors of metabolism such as phenylketonuria.
  • compositions can contain one or more amino acids which have a bitter or metallic taste or aftertaste.
  • amino acids include, for example, but are not limited to, an essential amino acid such as L isomers of leucine, isoleucine, histidine, lysine, methionine, phenylalanine, threonine, tryptophan, tyrosine and valine.
  • Dental hygienic compositions are known in the art and include, for example, but not limited to, a toothpaste, a mouthwash, a plaque rinse, a dental floss, a dental pain reliever (such as ANBESOL) and the like.
  • the dental hygienic composition includes one natural sweetener.
  • the dental hygienic composition includes more than one natural sweetener.
  • the dental hygienic composition includes sucrose and corn syrup, or sucrose and aspartame.
  • a cosmetic product includes, for example, but not limited to, a face cream, a lipstick, a lip gloss and the like.
  • Other suitable cosmetic products of use in this invention include a lip balm, such as CHAPSTICK or BURT'S BEESWAX Lip Balm.
  • the present invention also provides methods for enhancing the sweetness of a flavoring with modifying properties and decreasing its use level in a consumable by incorporating ligustrosidic acid or a derivative thereof.
  • the invention provides a consumable containing an olfactory effective amount of ligustrosidic acid or a derivative hereof and a flavoring with modifying properties in a reduced amount in order to achieve the same level of sweetness when the flavoring with modifying properties is used alone in a traditional amount.
  • the amount of flavoring with modifying properties used in a consumable can be reduced by at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 95%, from about 60% to about 99% or from about 20% to about 50%.
  • ligustrosidic acid or a derivative thereof can be used in a consumable as a sweetness enhancer, which retains a desired sweetness but contains lower amounts of a natural sweetener or an artificial sweetener.
  • an improved carbonated soft drink can be produced with the same sweetness as the known carbonated soft drink but with lower sugar content by adding ligustrosidic acid or a derivative thereof.
  • Additional materials can also be used in conjunction with ligustrosidic acid or a derivative thereof of the present invention to encapsulate and/or deliver the lingering aftertaste masking effect.
  • Some well-known materials are, for example, but not limited to, polymers, oligomers, other non-polymers such as surfactants, emulsifiers, lipids including fats, waxes and phospholipids, organic oils, mineral oils, petrolatum, natural oils, perfume fixatives, fibers, starches, sugars and solid surface materials such as zeolite and silica.
  • Some preferred polymers include polyacrylate, polyurea, polyurethane, polyacrylamide, polyester, polyether, polyamide, poly(acrylate-co-acrylamide), starch, silica, gelatin and gum Arabic, alginate, chitosan, polylactide, poly(melamine-formaldehyde), poly(urea-formaldehyde), or a combination thereof.
  • Carica papaya leave extract was purchased (AuNutra® Industries Inc., California, U.S.). Among different batches, ligustrosidic acid, 2′-hydroxy ligustrosidic acid, verbascoside and isoverbascoside were identified, ranging from ⁇ 0.1-1%, from ⁇ 0.2-2%, from ⁇ 0.2-2% and from ⁇ 0.01-0.4%, respectively. Further fractionation was performed using high performance liquid chromatography (HPLC) to provide ligustrosidic acid at ⁇ 95% purity. In addition, 2′-hydroxy ligustrosidic acid was purchased.
  • HPLC high performance liquid chromatography
  • a sucrose solution (4%) was prepared in water.
  • Each of ligustrosidic acid and 2′-hydroxy ligustrosidic acid solutions of different concentrations was prepared in ethanol solution in water (50%).
  • Ligustrosidic acid and 2′-hydroxy ligustrosidic acid were evaluated at 1 and 200 ppm, respectively. Both were devoid of taste and smell.
  • Ligustrosidic acid exhibited particularly strong effect. When used with sucrose, ligustrosidic acid enhanced overall sweetness, body and mouthfeel. 2′-Hydroxy ligustrosidic acid exhibited strong effect in sweetness enhancement.
  • Luo Han Guo (Biovittoria Ltd., New Zealand) solution was prepared in water (120 ppm). Ligustrosidic acid and 2′-hydroxy ligustrosidic acid solutions were prepared as above (EXAMPLE II). The flavor profile of the Luo Han Guo solution with added ligustrosidic acid and 2′-hydroxy ligustrosidic acid is reported in the following:
  • Ligustrosidic acid exhibited particularly strong effect. When used with Luo Han Guo, ligustrosidic acid enhanced overall sweetness, body and mouthfeel. 2′-Hydroxy ligustrosidic acid exhibited strong effect in sweetness enhancement.
  • the sucrose solution (4%) with the addition of various amount of Carica papaya leave extract was evaluated.
  • the flavor profile is as follows:
  • Sample Extract (ppm) Flavor Profile 1 0 (Base) Mild in sweet perception 2 1 Very slight effect, started to display the perception of sugary syrup, slightly botanical, slightly enhanced mouthfeel 3 10 Natural fruit juice-like 4 20 Caramelized sugar-like, viscous mouthfeel 5 50 Long lasting and enhanced sweetness, pleasant sugary mouthfeel, sugar distillate-like 6 100 Maple syrup-like, brown and cooked sugar-like, mouth coating 7 200 More botanical and fruity sweetness, started to display off-taste and astringent note 8 500 More off-taste and astringent note started to overpower sweetness 9 1000 Woody, barky and astringent notes overpowered sweetness
  • Carica papaya leave extract enhanced sucrose mouthfeel starting at 1 ppm and sucrose sweetness at 10 ppm. However, undesirable off-taste started to develop at 500 ppm.
  • the fructose solution (3.4%) with the addition of various amount of Carica papaya leave extract was evaluated.
  • the flavor profile is as follows:
  • Sample Extract (ppm) Flavor Profile 1 0 (Base) Mild in sweet perception 2 1 Slightly enhanced mouthfeel, slightly more mouth coating 3 10 More fruity, added body 4 20 Started to become sucrose-like, more body, more fullness 5 50 More sucrose-like, viscous, more mouth coating 6 100 Maple syrup-like, more mouth coating 7 200 Started to display off-taste and astringent note 8 500 More off-taste and astringent note started to overpower sweetness 9 1000 Woody, barky and astringent notes overpowered sweetness
  • Carica papaya leave extract provided sucrose-like flavor profile.
  • Carica papaya leave extract enhanced fructose sweetness, body and mouthfeel at all levels tested. However, undesirable off-taste started to develop at 500 ppm.
  • the Luo Han Guo solution 120 ppm
  • Carica papaya leave extract was evaluated.
  • the flavor profile is as follows:
  • Sample Extract (ppm) Flavor Profile 1 0 (Base) Mild in sweet perception 2 1 Some mouthfeel 3 10 Earlier onset sweetness, persistent mouthfeel helped to suppress bitterness 4 20 Upfront sweetness, upfront mouthfeel 5 50 pleasant sweetness, less lingering bitterness, mouthfeel helped to suppress off-taste 6 100 Clear effect, more sucrose-like, less off-taste 7 200 Started to display off-taste 8 500 More off-taste started to overpower sweetness 9 1000 Woody, barky and astringent notes overpowered sweetness
  • Carica papaya leave extract provided sucrose-like flavor profile.
  • Carica papaya leave extract enhanced Luo Han Guo sweetness and masked lingering bitterness. However, undesirable off-taste started to develop at 500 ppm.
  • the Reb A solution (90 ppm) with the addition of various amount of Carica papaya leave extract was evaluated.
  • the flavor profile is as follows:
  • Sample Extract (ppm) Flavor Profile 1 0 (Base) Mild in sweet perception 2 1 Very slight effect 3 10 Slightly earlier onset of sweet perception, slightly increased mouthfeel, more body, less peakiness 4 20 Clear effect, enhanced sugary mouthfeel, more body, less lingering bitterness, less stevia's off-taste 5 50 Fruity sweetness, apple juice-like, enhanced mouthfeel 6 100 Sucrose-like, even more mouth fullness, pleasant mouthcoating 7 200 Started to display off-taste 8 500 Woody and barky, still less stevia's off-taste, maple syrup-like 9 1000 Woody and barky, still less stevia's off-taste, maple syrup-like
  • Carica papaya leave extract enhanced Reb A sweetness and mouthfeel, and masked lingering bitterness and off-taste. However, undesirable off-taste started to develop at 500 ppm.
  • the GSG Glucosyl Steviol Glucosides solution (200 ppm) with the addition of various amount of Carica papaya leave extract was evaluated.
  • the flavor profile is as follows:
  • Sample Extract (ppm) Flavor Profile 1 0 (Base) Mild in sweet perception 2 1 Minimal effect 3 10 Very slight effect on sweetness, more mouthfeel 4 20 Very slight effect on sweetness, more mouthfeel 5 50 More sweetness, clearly enhanced mouthfeel 6 100 Enhanced sweetness and mouthfeel 7 200 Maple syrup-like with sugary mouthfeel, started to display astringent note 8 500 Maple syrup-like, astringent 9 1000 Woody and barky
  • Carica papaya leave extract enhanced glucosyl steviol glucosides sweetness and mouthfeel. However, undesirable off-taste started to develop at 500 ppm.
  • a Dannon Non-Fat Plain Yogurt with 6% sucrose was prepared and used as the base. Different amount of Carica papaya leave extract was added to the base. Flavor profile was evaluated and is as follows:
  • Sample Extract (ppm) Flavor Profile 1 0 (Base) Mild in sweet perception 2 1 Slightly more and lingering sweetness, less sour perception 3 10 More sweetness 4 20 Upfront sweetness, jammy, creamy, mouthwatering and pleasant, waxy and cardboard-like notes decreased 5 50 Cooked sugar-like 6 100 Sweet, mouth coating and thick, less sourness 7 200 Intense sweetness, viscous, slight brown sugar note developed 8 500 Maple syrup-like, woody 9 1000 Woody and barky, more brown sugar note developed
  • Carica papaya leave extract enhanced the sweetness of sucrose-containing yogurt and reduced its sourness. However, undesirable off-taste started to develop at 1000 ppm.
  • a Dannon Plain Nonfat Yogurt with GSG 600 pm was prepared and used as the base. Different amount of Carica papaya leave extract was added to the base. Flavor profile was evaluated and is as follows:
  • Flavor Profile 1 0 (Base) Mild in sweet perception 2 1 Less sour perception 3 10 Slightly enhanced mouthfeel, less sourness and less steviol's off-taste 4 20 Enhanced upfront sweetness, rounded flavor profile 5 50 Enhanced upfront sweetness, mouthwatering, less steviol's off-taste, pleasant 6 100 Less steviol's off-taste 7 200 Slight brown sugar note developed, cooked sugar-like 8 500 Maple syrup-like 9 1000 Woody and barky
  • Carica papaya leave extract enhanced the sweetness and mouthfeel of GSG-containing yogurt.
  • Sample Extract (ppm) Flavor Profile 1 0 (Base) Mild in sweet perception 2 1 Intense sweetness and mouthfeel, creamier 3 10 More sweetness, more natural strawberry flavor, creamier, more fat perception, less plastic-like note 4 20 More and lingering sweetness, creamier, more fat perception 5 50 Significant mouth coating, more fat perception 6 100 Upfront sweetness 7 200 More overall sweetness, pleasant with no off-taste of the extract 8 500 Maple syrup-like sweetness 9 1000 Brown sugar-like, barky note overpowered the base flavor
  • Carica papaya leave extract enhanced the sweetness and mouthfeel of cane sugar-containing yogurt at all levels tested.

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Abstract

The use of ligustrosidic acid or a derivative thereof to enhance the sweetness of a sweetness modifier and to decrease the amount of a sweetness modifier used in a consumable is provided.

Description

    BACKGROUND OF INVENTION
  • Reducing sugar content in food and beverages has become a necessity in the food industry. Food and beverage manufacturers generally use non-caloric, high-intensity sweetness modifiers, such as rebaudioside A (Reb A), aspartame, saccharin, glycosylated steviol glycosides, etc., to partially or completely replace sugar. However, these sweetness modifiers may exhibit undesirable taste attributes such as delayed onset of sweetness, bitter and astringent aftertaste, and lack of body and mouthfeel. Consequently, sweetness enhancers have become valuable tools, which reduce the use of sugar and/or sweetness modifiers, in achieving the desired sweetness intensity and mouthfeel with reduced off-taste.
  • Sweetness enhancers have been described in the prior art. For example, WO 2013/143822 teaches the use of adenosine as sweetness enhancer for certain sugars; EP 2606747 describes the use of deoxycholic acid or a derivative thereof for enhancing the sweetness of consumables; WO 2013/077668 describes the sweetness enhancing effect of a glycan or glycopeptide derived from soy sauce; WO 2012/107203 teaches the use of nobiletin or a derivative or a hydrate thereof as a sweetener or sweetness enhancer; WO 2009/023975 describes the use of iso-mogroside V as a sweetener and sweetness enhancer; US 2008/0242740 teaches aroma compositions of alkamides with hesperetin and/or 4-hydroxydihydrochalcones for enhancing sweet sensory impressions; and WO 2007/014879 and WO 2007/107596 respectively teach the use of hesperetin and 4-hydroxydihydrochalcones for enhancing the sweet taste of a sweet-tasting substance or sweet olfactory impression of a flavoring.
    • SUMMARY OF THE INVENTION
  • This invention provides a method of enhancing the sweetness of a sweetness modifier by adding an olfactory effective amount of ligustrosidic acid or a derivative thereof.
  • Ligustrosidic acid and its derivative, 2′-hydroxy ligustrosidic acid, are represented by formulas set forth below:
  • Figure US20210251267A1-20210819-C00001
  • In one embodiment, the present invention is directed to a method of enhancing the sweetness of a sweetness modifier comprising the step of adding an olfactory effective amount of ligustrosidic acid or a derivative thereof.
  • In another embodiment, the present invention is directed to a method enhancing the sweetness of a sweetness modifier comprising the step of adding an olfactory effective amount of Carica papaya leave extract.
  • In another embodiment, the present invention is directed to a composition comprising a sweetness modifier and an olfactory effective amount of ligustrosidic acid or a derivative thereof.
  • In another embodiment, the present invention is directed to a composition comprising a sweetness modifier and an olfactory effective amount of Carica papaya leave extract.
  • In another embodiment, the present invention is directed to a consumable comprising a sweetness modifier and an olfactory effective amount of ligustrosidic acid or a derivative thereof.
  • In another embodiment, the present invention is directed to a consumable comprising a sweetness modifier and an olfactory effective amount of Carica papaya leave extract.
  • These and other embodiments of the present invention will be apparent by reading the following specification.
    • DETAILED DESCRIPTION OF THE INVENTION
  • Ligustrosidic acid, [3-(carboxymethylene)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)]-2H-pyran-4-acetic acid-α-[2-(4-hydroxyphenyl)ethyl]ester, and its derivative, 2′-hydroxy ligustrosidic acid, are naturally constituents in Ligustrum lucidum Ait and Ligustrum japonicum. 2′-Hydroxy ligustrosidic acid was also reported in genus Cyperus and olive (Li et al., Molecules (2017), 22(5): 689; Gao et al., Records of Natural Products (2015), 9(3): 323-328; Kikuchi et al., Yakugaku Zasshi (1985), 105(2): 142-147; Gao et al., Chemistry of Natural Compounds (2017), 53(3): 553-554; Cheng et al., Article in Asian Journal of Chemistry (2014), 26(13): 3967-3970; Rubio-Senent et al., Journal of agricultural and food chemistry (2013), 61(6): 1235-1248).
  • Ligustrum lucidum Ait has been used as a traditional Chinese medicine over thousands of years in invigorating liver and kidney (Hu et al., Oncology Reports (2014), 32(3):1037-1042). Other species such as Ligustrum liukiuense, Ligustrum lucidum, Ligustrum morrisonense, Ligustrum pricei, and Ligustrum sinense have been widely used as tea or herbal medicine in Europe, China and Japan (Wu et al. Food Chemistry (2011), 127(2), 564-571). The extract of Ligustrum sinense was also evaluated in a combined treatment of Pseudomonas aeruginosa PA01 biofilm formation with gentamicin sulphate (Yang et al. Journal of environmental biology (2013), 34(2 Spec No), 451-457). Thus, it has been suggested but not proven that 2′-hydroxy ligustrosidic acid may possess antioxidant function (Gao et al., Records of Natural Products (2015), 9(3): 323-328; Gao et al., Chemistry of Natural Compounds (2017), 53(3): 553-554). However, no function has ever been reported or even suggested for ligustrosidic acid.
  • In the present invention, ligustrosidic acid and 2′-hydroxy ligustrosidic acid have been for the first time identified in genus Carica. Further, ligustrosidic acid and 2′-hydroxy ligustrosidic acid have also been found to possess an unexpected and advantageous use in food. In particular, ligustrosidic acid, 2′-hydroxy ligustrosidic acid, a salt thereof or a mixture thereof has been found to enhance the sweetness of sweetness modifiers without undesirable off-notes.
  • Accordingly, the present invention provides a method of using ligustrosidic acid, 2′-hydroxy ligustrosidic acid, a salt thereof or a mixture thereof to enhance the sweetness of a sweetness modifier and decrease the amount of a sweetness modifier used in a consumable.
  • The term “ligustrosidic acid or a derivative thereof” is understood to mean ligustrosidic acid, 2′-hydroxy ligustrosidic acid, a salt thereof or a mixture thereof.
  • In the present invention, ligustrosidic acid and 2′-hydroxy ligustrosidic acid are available commercially and can also be an isolated and purified form a botanical extract, for example, genus Ligustrum such as Ligustrum amamianum, Ligustrum amurense, Ligustrum angustum, Ligustrum australianum, Ligustrum chenaultii, Ligustrum compactum, Ligustrum confusum, Ligustrum delavayanum, Ligustrum expansum, Ligustrum gracile, Ligustrum henryi, Ligustrum ibota, Ligustrum indicum, Ligustrum japonicum, Ligustrum leucanthum, Ligustrum lianum, Ligustrum liukiuense, Ligustrum longitubum, Ligustrum lucidum, Ligustrum massalongianum, Ligustrum micranthum, Ligustrum microcarpum, Ligustrum morrisonense, Ligustrum obovatilimbum, Ligustrum obtusifolium, Ligustrum ovalifolium, Ligustrum pedunculare, Ligustrum pricei, Ligustrum punctifolium, Ligustrum quihoui, Ligustrum retusum, Ligustrum robustum, Ligustrum sempervirens, Ligustrum sinense, Ligustrum strongylophyllum, Ligustrum tenuipes, Ligustrum tschonoskii, Ligustrum vulgare, Ligustrum xingrenense and Ligustrum yunguiense, genus Cyperus such as Cyperus rotundus, genus Olea such as Olea europaea and genus Carica such as Carica baccata, Carica candamarcensis, Carica candicans, Carica caudata, Carica cauliflora, Carica cestriflora, Carica chilensis, Carica crassipetala, Carica cundinamarcensis, Carica dodecaphylla, Carica glandulosa, Carica goudotiana, Carica heterophylla, Carica horovitziana, Carica longiflora, Carica Mexicana, Carica microcarpa, Carica monoica, Carica nana, Carica omnilingua, Carica palandensis, Carica parviflora, Carica pentagona, Carica pubescens, Carica pulchra, Carica quercifolia, Carica sphaerocarpa, Carica spinose, Carica sprucei, Carica stipulate and Carica weberbaueri. A salt form, for example, includes ligustrosidic acid methyl ester.
  • If provided as a botanical extract, preferably the extract is enriched for ligustrosidic acid and 2′-hydroxy ligustrosidic acid to achieve a content of about 0.01% and greater, respectively. For example, the botanical extract contains each of ligustrosidic acid and 2′-hydroxy ligustrosidic acid from about 0.05% to about 95%, from about 0.1% to about 50% or from about 0.2% to about 10%. Unless otherwise specified, percentages (% s) are by weight.
  • A natural sweetener includes, for example, but not limited to, sucrose, fructose, glucose, high fructose corn syrup, Stevia rebaudiana compositions including pure components of Reb A, stevioside, and rebaudioside D (Reb D), xylose, arabinose, or rhamnose, as well as sugar alcohols such as erythritol, xylitol, mannitol, sorbitol, inositol and a combination thereof. An artificial sweetener includes, for example, but not limited to, aspartame, sucralose, neotame, acesulfame potassium, saccharin and a combination thereof.
  • A flavoring is a preparation that provides a consumable with a particular taste and/or smell. A flavoring with modifying properties is a subset of the flavoring. It is added to the consumable to reduce off-notes and/or improve overall profile. The flavorings with modifying properties of the present invention include, for example, but not limited to, a Stevia composition including stevioside, steviolbioside Reb A, rebaudioside B (Reb B), rebaudioside C (Reb C), Reb D, rebaudioside E (Reb E), rebaudioside F (Reb F), dulcoside A, dulcoside B, rubusoside, alpha-glucosyl Stevia, fructosyl Stevia, galactosyl Stevia, beta-glucosyl Stevia, siamenoside, mogrosidc IV, mogroside V, Luo Han Guo, monatin, glycyrrhizic acid, thaumatin, a salt thereof, a glycosylated derivative thereof and a combination thereof. The glycosylated derivatives can be prepared via transglycosylation reactions with, for example, but not limited to, glucose, fructose, galactose, rhamnose, ribose, mannose, arabinose, fucose, maltose, lactose, sucrose, rutinose, sorbose, xylulose, ribulose, rhammulose and xylose. In one embodiment, the flavorings with modifying properties of the present invention include Reb A, Reb C, rubusoside, Reb D, mogroside V, Luo Han Guo, monatin acid, a salt thereof, a glycosylated derivative thereof and a combination thereof. The flavorings with modifying properties of the present invention exhibit weak intrinsic sweetness. Some other flavorings of the present invention include, for example, but not limited to, curculin, monellin, mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobtain, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, cyclocarioside I and a combination thereof.
  • Accordingly, the term “a sweetness modifier” of the present invention refers to a sweetener including a natural sweetener and an artificial sweetener or a flavoring with modifying properties set forth in the above.
  • The term “sweetness” or “sweetness intensity” is understood to mean the relative strength of sweet sensation as observed or experienced by an individual, e.g., a human, or a degree or amount of sweetness detected by a taster, for example on the scale from 0 (none) to 8 (very strong) used in sensory evaluations according to the procedure described in American Society for Testing Materials, Special Technical Publication-434: “Manual on Sensory Testing Methods,” ASTM International, West Conshohocken, Pa. (1996).
  • The term “olfactory effective amount” is understood to mean the amount of ligustrosidic acid or a derivative thereof used in a combination with a sweetness modifier, wherein ligustrosidic acid or a derivative thereof enhances the sweetness of the sweetness modifier. Its olfactory effective amount may vary depending on many factors including other ingredients, their relative amounts and the olfactory effect that is desired. Any amount of ligustrosidic acid or a derivative thereof that provides the desired degree of sweetness enhancement without exhibiting off-taste can be used. In certain embodiments, the olfactory effective amount ranges from about 1 ppb to about 1000 ppm by weight, preferably from about 5 ppb to about 100 ppm by weight and more preferably from about 10 ppb to about 10 ppm by weight. When used in the form of a botanical extract such as Carica papaya leave extract, the olfactory effective amount ranges from about 100 ppb to about 1000 ppm by weight, preferably from about 1 to about 500 ppm by weight and more preferably from about 5 to about 200 ppm.
  • A consumable includes, for example, a food product (e.g., a beverage), a sweetener such as a natural sweetener or an artificial sweetener, a pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition and a cosmetic product. The consumable may further contain a flavoring.
  • In some embodiments, a consumable is a food product including, for example, but not limited to, fruits, vegetables, juices, meat products such as ham, bacon and sausage, egg products, fruit concentrates, gelatins and gelatin-like products such as jams, jellies, preserves and the like, milk products such as yogurt, ice cream, sour cream and sherbet, icings, syrups including molasses, corn, wheat, rye, soybean, oat, rice and barley products, nut meats and nut products, cakes, cookies, confectionaries such as candies, gums, fruit flavored drops, and chocolates, chewing gums, mints, creams, pies and breads. In a certain embodiment, the food product is a beverage including, for example, but not limited to, coffee, tea, carbonated soft drinks, such as COKE and PEPSI, non-carbonated soft drinks and other fruit drinks, sports drinks such as GATORADE and alcoholic beverages such as beers, wines and liquors. A consumable also includes prepared packaged products, such as granulated flavor mixes, which upon reconstitution with water provide non-carbonated drinks, instant pudding mixes, instant coffee and tea, coffee whiteners, malted milk mixes, pet foods, livestock feed, tobacco, and materials for baking applications, such as powdered baking mixes for the preparation of breads, cookies, cakes, pancakes, donuts and the like. A consumable also includes diet or low-calorie food and beverages containing little or no sucrose. A preferred consumable includes carbonated beverages. Consumables further include condiments such as herbs, spices and seasonings, flavor enhancers (e.g., monosodium glutamate), dietetic sweeteners and liquid sweeteners.
  • In other embodiments, a consumable is a pharmaceutical composition, a dietary supplement, a nutraceutical, a dental hygienic composition or a cosmetic product. Preferred compositions are pharmaceutical compositions containing ligustrosidic acid or a derivative thereof, one or more pharmaceutically acceptable excipients, and one or more active agents that exert a biological effect other than sweetness enhancement. Such active agents include pharmaceutical and biological agents that have an activity other than taste enhancement. Such active agents are well known in the art (See, e.g., The Physician's Desk Reference). Such compositions can be prepared according to procedures known in the art, for example, as described in Remington's Pharmaceutical Sciences, Mack Publishing Co., Easton, Pa. In one embodiment, such an active agent includes a bronchodilator, an anorexiant, an antihistamine, a nutritional supplement, a laxative, an analgesic, an anesthetic, an antacid, a H2-receptor antagonist, an anticholinergic, an antidiarrheal, a demulcent, an antitussive, an antinauseant, an antimicrobial, an antibacterial, an antifungal, an antiviral, an expectorant, an anti-inflammatory agent, an antipyretic and a mixture thereof. In another embodiment, the active agent is selected from the group consisting of an antipyretic and analgesic, e.g., ibuprofen, acetaminophen or aspirin, a laxative, e.g., phenolphthalein dioctyl sodium sulfosuccinate, an appetite depressant, e.g., an amphetamine, phenylpropanolamine, phenylpropanolamine hydrochloride, or caffeine, an antacid, e.g., calcium carbonate, an antiasthmatic, e.g., theophylline, an antidiarrheal, e.g., diphenoxylate hydrochloride, an agent against flatulence, e.g., simethecon, a migraine agent, e.g., ergotamine tartrate, a psychopharmacological agent, e.g., haloperidol, a spasmolytic or sedative, e.g., phenobarbital, an antihyperkinetic, e.g., methyldopa or methylphenidate, a tranquilizer, e.g., a benzodiazepine, hydroxyzine, meprobramate or phenothiazine, an antihistaminic, e.g., astemizol, chlorpheniramine maleate, pyridamine maleate, doxlamine succinate, brompheniramine maleate, phenyltoloxamine citrate, chlorcyclizine hydrochloride, pheniramine maleate, or phenindamine tartrate, a decongestant, e.g., phenylpropanolamine hydrochloride, phenylephrine hydrochloride, pseudoephedrine hydrochloride, pseudoephedrine sulfate, phenylpropanolamine bitartrate, or ephedrine, a beta-receptor blocker, e.g., propranolol, an agent for alcohol withdrawal, e.g., disulfuram, an antitussive, e.g., benzocaine, dextromethorphan, dextromethorphan hydrobromide, noscapine, carbetapentane citrate, and chlophedianol hydrochloride, a fluorine supplement, e.g., sodium fluoride, a local antibiotic, e.g., tetracycline or clindamycin, a corticosteroid supplement, e.g., prednisone or prednisolone; an agent against gout, e.g., colchicine or allopurinol, an antiepileptic, e.g., phenytoin sodium, an agent against dehydration, e.g., electrolyte supplements, an antiseptic, e.g., cetylpyridinium chloride, a NSAID, e.g., acetaminophen, ibuprofen, naproxen, or a salt thereof, a gastrointestinal active agent, e.g., loperamide and famotidine, an alkaloid, e.g., codeine phosphate, codeine sulfate, or morphine, a supplement for trace elements, e.g., sodium chloride, zinc chloride, calcium carbonate, magnesium oxide, and other alkali metal salts and alkali earth metal salts; a vitamin, an ion-exchange resin, e.g., cholestyramine, a cholesterol-depressant and lipid-lowering substance, an antiarrhythmic, e.g., N-acetylprocainamide and an expectorant, e.g., guaifenesin. Examples of dietary supplements or nutraceuticals include, for example, but are not limited to, an enteral nutrition product for treatment of nutritional deficit, trauma, surgery, Crohn's disease, renal disease, hypertension, obesity and the like, to promote athletic performance, muscle enhancement or general well-being or inborn errors of metabolism such as phenylketonuria. In particular, such compositions can contain one or more amino acids which have a bitter or metallic taste or aftertaste. Such amino acids include, for example, but are not limited to, an essential amino acid such as L isomers of leucine, isoleucine, histidine, lysine, methionine, phenylalanine, threonine, tryptophan, tyrosine and valine. Dental hygienic compositions are known in the art and include, for example, but not limited to, a toothpaste, a mouthwash, a plaque rinse, a dental floss, a dental pain reliever (such as ANBESOL) and the like. In one embodiment, the dental hygienic composition includes one natural sweetener. In another embodiment, the dental hygienic composition includes more than one natural sweetener. In yet another embodiment, the dental hygienic composition includes sucrose and corn syrup, or sucrose and aspartame. A cosmetic product includes, for example, but not limited to, a face cream, a lipstick, a lip gloss and the like. Other suitable cosmetic products of use in this invention include a lip balm, such as CHAPSTICK or BURT'S BEESWAX Lip Balm.
  • In addition, the present invention also provides methods for enhancing the sweetness of a flavoring with modifying properties and decreasing its use level in a consumable by incorporating ligustrosidic acid or a derivative thereof. In one embodiment, the invention provides a consumable containing an olfactory effective amount of ligustrosidic acid or a derivative hereof and a flavoring with modifying properties in a reduced amount in order to achieve the same level of sweetness when the flavoring with modifying properties is used alone in a traditional amount. In this respect, the amount of flavoring with modifying properties used in a consumable can be reduced by at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 95%, from about 60% to about 99% or from about 20% to about 50%.
  • As indicated, ligustrosidic acid or a derivative thereof can be used in a consumable as a sweetness enhancer, which retains a desired sweetness but contains lower amounts of a natural sweetener or an artificial sweetener. For example, an improved carbonated soft drink can be produced with the same sweetness as the known carbonated soft drink but with lower sugar content by adding ligustrosidic acid or a derivative thereof.
  • Additional materials can also be used in conjunction with ligustrosidic acid or a derivative thereof of the present invention to encapsulate and/or deliver the lingering aftertaste masking effect. Some well-known materials are, for example, but not limited to, polymers, oligomers, other non-polymers such as surfactants, emulsifiers, lipids including fats, waxes and phospholipids, organic oils, mineral oils, petrolatum, natural oils, perfume fixatives, fibers, starches, sugars and solid surface materials such as zeolite and silica. Some preferred polymers include polyacrylate, polyurea, polyurethane, polyacrylamide, polyester, polyether, polyamide, poly(acrylate-co-acrylamide), starch, silica, gelatin and gum Arabic, alginate, chitosan, polylactide, poly(melamine-formaldehyde), poly(urea-formaldehyde), or a combination thereof.
  • The following are provided as specific embodiments of the present invention. Other modifications of this invention will be readily apparent to those skilled in the art. Such modifications are understood to be within the scope of this invention. Materials were purchased from Aldrich Chemical Company unless noted otherwise. As used herein all percentages are weight percent unless otherwise noted, ppm is understood to stand for parts per million, L is understood to be liter, mL is understood to be milliliter, g is understood to be gram, Kg is understood to be kilogram, mol is understood to be mole, mmol is understood to be millimole, psig is understood to be pound-force per square inch gauge, and mmHg be millimeters (mm) of mercury (Hg). IFF as used in the examples is understood to mean International Flavors & Fragrances Inc., New York, N.Y., USA.
    • Example I: Preparation of Test Samples
  • Carica papaya leave extract was purchased (AuNutra® Industries Inc., California, U.S.). Among different batches, ligustrosidic acid, 2′-hydroxy ligustrosidic acid, verbascoside and isoverbascoside were identified, ranging from ˜0.1-1%, from ˜0.2-2%, from ˜0.2-2% and from ˜0.01-0.4%, respectively. Further fractionation was performed using high performance liquid chromatography (HPLC) to provide ligustrosidic acid at ˜95% purity. In addition, 2′-hydroxy ligustrosidic acid was purchased.
    • Example II: Enhancement of Sucrose Sweetness
  • A sucrose solution (4%) was prepared in water. Each of ligustrosidic acid and 2′-hydroxy ligustrosidic acid solutions of different concentrations was prepared in ethanol solution in water (50%). Ligustrosidic acid and 2′-hydroxy ligustrosidic acid were evaluated at 1 and 200 ppm, respectively. Both were devoid of taste and smell.
  • The flavor profile of the sucrose solution with added ligustrosidic acid and 2′-hydroxy ligustrosidic acid is reported in the following:
  • Compound Ligustrosidic Acid (ppm) 2′-Hydroxy Ligustrosidic Acid (ppm)
    Concentration 0.155 0.310 0.620 0.160 0.320 0.640
    (ppm)
    Flavor Profile Enhanced Strong, Enhanced Slightly Upfront Enhanced
    sweetness sucrose flavor but enhanced and lasting flavor but
    and syrup-like impact sweetness sweetness, impact
    mouthfeel, sweetness, started to without pleasant started to
    fuller body much fuller level off much level off
    with body with impact on
    increased glycerin-like mouthfeel
    viscosity heaviness
  • Ligustrosidic acid exhibited particularly strong effect. When used with sucrose, ligustrosidic acid enhanced overall sweetness, body and mouthfeel. 2′-Hydroxy ligustrosidic acid exhibited strong effect in sweetness enhancement.
    • Example III: Enhancement of Luo Han Guo Sweetness
  • A Luo Han Guo (Biovittoria Ltd., New Zealand) solution was prepared in water (120 ppm). Ligustrosidic acid and 2′-hydroxy ligustrosidic acid solutions were prepared as above (EXAMPLE II). The flavor profile of the Luo Han Guo solution with added ligustrosidic acid and 2′-hydroxy ligustrosidic acid is reported in the following:
  • Compound
    Ligustrosidic Acid (ppm) 2′-Hydroxy Ligustrosidic Acid (ppm)
    Concentration (ppm)
    0.155 0.310 0.620 0.160 0.320 0.640
    Flavor Profile More Significantly Very heavy Slightly Sugar-like Increased
    sugar-like increased and syrup- enhanced sweetness sweetness
    and less body fullness, like profile, sweetness without
    licorice- upfront less off- without much
    like sweetness, taste, an much impact on
    sweetness, more sugar- undesirable impact on mouthfeel
    upfront like and less suppression mouthfeel,
    mouthfeel, licorice-like, of sweetness licorice-like
    fuller body less tingling appeared sweetness
    off-taste remained
  • Ligustrosidic acid exhibited particularly strong effect. When used with Luo Han Guo, ligustrosidic acid enhanced overall sweetness, body and mouthfeel. 2′-Hydroxy ligustrosidic acid exhibited strong effect in sweetness enhancement.
    • Example IV: Preparation of Test Solutions
  • The effect of botanical extract such as Carica papaya leave extract on sweetness was examined. Solutions of Carica papaya leave extract containing ligustrosidic acid (0.61%), 2′-hydroxy ligustrosidic acid (0.62%), verbascoside (0.69%) and isoverbascoside (0.21%) were prepared in ethanol solution in water (50%) to obtain a series of concentrations ranging from 1 to 1000 ppm.
  • Solutions of sucrose (4%) and Luo Han Guo (120 ppm) were prepared as above (EXAMPLE II and III). In addition, solutions of fructose (3.4%), Reb A (GLG Life Tech Corporation, Canada) (90 ppm) and GSG (Glucosyl Steviol Glucosides, GLG Life Tech Corporation, Canada) (200 ppm) were also prepared in water.
  • The sweetness enhancement of (i) sucrose, (ii) Luo Han Guo, (iii) fructose, (iv) Reb A and (v) GSG by Carica papaya leave extract was evaluated, respectively. In all groups tested, Carica papaya leave extract enhanced sweetness.
    • Example V: Enhancement of Sucrose Sweetness by Botanical Extract
  • The sucrose solution (4%) with the addition of various amount of Carica papaya leave extract was evaluated. The flavor profile is as follows:
  • Sample  Extract (ppm) Flavor Profile
    1     0 (Base) Mild in sweet perception
    2 1 Very slight effect, started to display the perception of sugary syrup,
    slightly botanical, slightly enhanced mouthfeel
    3 10  Natural fruit juice-like
    4 20  Caramelized sugar-like, viscous mouthfeel
    5 50  Long lasting and enhanced sweetness, pleasant sugary mouthfeel,
    sugar distillate-like
    6 100   Maple syrup-like, brown and cooked sugar-like, mouth coating
    7 200   More botanical and fruity sweetness, started to display off-taste and
    astringent note
    8 500   More off-taste and astringent note started to overpower sweetness
    9 1000    Woody, barky and astringent notes overpowered sweetness
  • Carica papaya leave extract enhanced sucrose mouthfeel starting at 1 ppm and sucrose sweetness at 10 ppm. However, undesirable off-taste started to develop at 500 ppm.
    • Example VI: Enhancement of Fructose Sweetness by Botanical Extract
  • The fructose solution (3.4%) with the addition of various amount of Carica papaya leave extract was evaluated. The flavor profile is as follows:
  • Sample  Extract (ppm) Flavor Profile
    1     0 (Base) Mild in sweet perception
    2 1 Slightly enhanced mouthfeel, slightly more mouth coating
    3 10  More fruity, added body
    4 20  Started to become sucrose-like, more body, more fullness
    5 50  More sucrose-like, viscous, more mouth coating
    6 100   Maple syrup-like, more mouth coating
    7 200   Started to display off-taste and astringent note
    8 500   More off-taste and astringent note started to overpower sweetness
    9 1000    Woody, barky and astringent notes overpowered sweetness
  • Carica papaya leave extract provided sucrose-like flavor profile. Carica papaya leave extract enhanced fructose sweetness, body and mouthfeel at all levels tested. However, undesirable off-taste started to develop at 500 ppm.
    • Example VII: Enhancement of Luo Han Guo Sweetness by Botanical Extract
  • The Luo Han Guo solution (120 ppm) with the addition of various amount of Carica papaya leave extract was evaluated. The flavor profile is as follows:
  • Sample  Extract (ppm) Flavor Profile
    1     0 (Base) Mild in sweet perception
    2 1 Some mouthfeel
    3 10  Earlier onset sweetness, persistent
    mouthfeel helped to suppress bitterness
    4 20  Upfront sweetness, upfront mouthfeel
    5 50  Pleasant sweetness, less lingering bitterness,
    mouthfeel helped to suppress off-taste
    6 100   Clear effect, more sucrose-like, less off-taste
    7 200   Started to display off-taste
    8 500   More off-taste started to overpower sweetness
    9 1000    Woody, barky and astringent notes overpowered sweetness
  • Carica papaya leave extract provided sucrose-like flavor profile. Carica papaya leave extract enhanced Luo Han Guo sweetness and masked lingering bitterness. However, undesirable off-taste started to develop at 500 ppm.
    • Example VIII: Enhancement of Reb A Sweetness by Botanical Extract
  • The Reb A solution (90 ppm) with the addition of various amount of Carica papaya leave extract was evaluated. The flavor profile is as follows:
  • Sample  Extract (ppm) Flavor Profile
    1     0 (Base) Mild in sweet perception
    2 1 Very slight effect
    3 10  Slightly earlier onset of sweet perception, slightly increased
    mouthfeel, more body, less peakiness
    4 20  Clear effect, enhanced sugary mouthfeel, more body,
    less lingering bitterness, less stevia's off-taste
    5 50  Fruity sweetness, apple juice-like, enhanced mouthfeel
    6 100   Sucrose-like, even more mouth fullness, pleasant mouthcoating
    7 200   Started to display off-taste
    8 500   Woody and barky, still less stevia's off-taste, maple syrup-like
    9 1000    Woody and barky, still less stevia's off-taste, maple syrup-like
  • Carica papaya leave extract enhanced Reb A sweetness and mouthfeel, and masked lingering bitterness and off-taste. However, undesirable off-taste started to develop at 500 ppm.
    • Example IX: Enhancement of GSG Sweetness by Botanical Extract
  • The GSG (Glucosyl Steviol Glucosides) solution (200 ppm) with the addition of various amount of Carica papaya leave extract was evaluated. The flavor profile is as follows:
  • Sample  Extract (ppm) Flavor Profile
    1     0 (Base) Mild in sweet perception
    2 1 Minimal effect
    3 10  Very slight effect on sweetness, more mouthfeel
    4 20  Very slight effect on sweetness, more mouthfeel
    5 50  More sweetness, clearly enhanced mouthfeel
    6 100   Enhanced sweetness and mouthfeel
    7 200   Maple syrup-like with sugary mouthfeel,
    started to display astringent note
    8 500   Maple syrup-like, astringent
    9 1000    Woody and barky
  • Carica papaya leave extract enhanced glucosyl steviol glucosides sweetness and mouthfeel. However, undesirable off-taste started to develop at 500 ppm.
    • Example X: Sweetness Enhancement of Sucrose-Containing Yogurt
  • A Dannon Non-Fat Plain Yogurt with 6% sucrose was prepared and used as the base. Different amount of Carica papaya leave extract was added to the base. Flavor profile was evaluated and is as follows:
  • Sample  Extract (ppm) Flavor Profile
    1     0 (Base) Mild in sweet perception
    2 1 Slightly more and lingering sweetness, less sour perception
    3 10  More sweetness
    4 20  Upfront sweetness, jammy, creamy, mouthwatering and pleasant,
    waxy and cardboard-like notes decreased
    5 50  Cooked sugar-like
    6 100   Sweet, mouth coating and thick, less sourness
    7 200   Intense sweetness, viscous, slight brown sugar note developed
    8 500   Maple syrup-like, woody
    9 1000    Woody and barky, more brown sugar note developed
  • Carica papaya leave extract enhanced the sweetness of sucrose-containing yogurt and reduced its sourness. However, undesirable off-taste started to develop at 1000 ppm.
    • Example XI: Sweetness Enhancement of GSG-Containing Yogurt
  • A Dannon Plain Nonfat Yogurt with GSG (600 pm) was prepared and used as the base. Different amount of Carica papaya leave extract was added to the base. Flavor profile was evaluated and is as follows:
  • Sample  Extract (ppm) Flavor Profile
    1     0 (Base) Mild in sweet perception
    2 1 Less sour perception
    3 10  Slightly enhanced mouthfeel,
    less sourness and less steviol's off-taste
    4 20  Enhanced upfront sweetness,
    rounded flavor profile
    5 50  Enhanced upfront sweetness, mouthwatering,
    less steviol's off-taste, pleasant
    6 100   Less steviol's off-taste
    7 200   Slight brown sugar note developed,
    cooked sugar-like
    8 500   Maple syrup-like
    9 1000    Woody and barky
  • Carica papaya leave extract enhanced the sweetness and mouthfeel of GSG-containing yogurt.
    • Example XII: Sweetness Enhancement of Cane Sugar-Containing Yogurt
  • Different amount of Carica papaya leave extract was added to Dannon Danimals Smoothies Yogurt Drink (Strawberry Explosion), which contained 9% cane sugar. Flavor profile was evaluated and is as follows:
  • Sample  Extract (ppm) Flavor Profile
    1     0 (Base) Mild in sweet perception
    2 1 Intense sweetness and mouthfeel, creamier
    3 10  More sweetness, more natural strawberry flavor,
    creamier, more fat perception, less plastic-like note
    4 20  More and lingering sweetness, creamier, more fat perception
    5 50  Significant mouth coating, more fat perception
    6 100   Upfront sweetness
    7 200   More overall sweetness, pleasant with no off-taste of the extract
    8 500   Maple syrup-like sweetness
    9 1000    Brown sugar-like, barky note overpowered the base flavor
  • Carica papaya leave extract enhanced the sweetness and mouthfeel of cane sugar-containing yogurt at all levels tested.

Claims (20)

What is claimed is:
1. A method of enhancing the sweetness of a sweetness modifier comprising the step of adding an olfactory effective amount of ligustrosidic acid or a derivative thereof.
2. The method of claim 1, wherein the sweetness modifier is a sweetener.
3. The method of claim 2, wherein the sweetener is a natural sweetener selected from the group consisting of sucrose, fructose, glucose, high fructose corn syrup, rebaudioside A, stevioside, rebaudioside D, xylose, arabinose, rhamnose, erythritol, xylitol, mannitol, sorbitol, inositol and a combination thereof.
4. The method of claim 2, wherein the sweetener is an artificial sweetener selected from the group consisting of aspartame, sucralose, neotame, acesulfame potassium, saccharin and a combination thereof.
5. The method of claim 1, wherein the sweetness modifier is a flavoring with modifying properties selected from the group consisting of stevioside, steviolbioside rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, dulcoside B, rubusoside, alpha-glucosyl Stevia, fructosyl Stevia, galactosyl Stevia, beta-glucosyl Stevia, siamenoside, mogrosidc IV, mogroside V, Luo Han Guo, monatin, glycyrrhizic acid, thaumatin, a salt thereof, a glycosylated derivative thereof and a combination thereof.
6. The method of claim 1, wherein the olfactory effective amount is from about 1 ppb to about 1000 ppm.
7. The method of claim 1, wherein the olfactory effective amount is from about 5 ppb to about 100 ppm.
8. The method of claim 1, wherein the olfactory effective amount is from about 10 ppb to about 10 ppm.
9. The method of claim 1, wherein ligustrosidic acid or a derivative thereof is provided as a Carica papaya leave extract.
10. A composition comprising a sweetness modifier and an olfactory effective amount of ligustrosidic acid or a derivative thereof.
11. The composition of claim 10, wherein the sweetness modifier is a sweetener.
12. The composition of claim 11, wherein the sweetener is a natural sweetener selected from the group consisting of sucrose, fructose, glucose, high fructose corn syrup, rebaudioside A, stevioside, rebaudioside D, xylose, arabinose, rhamnose, erythritol, xylitol, mannitol, sorbitol, inositol and a combination thereof.
13. The composition of claim 11, wherein the sweetener is an artificial sweetener selected from the group consisting of aspartame, sucralose, neotame, acesulfame potassium, saccharin and a combination thereof.
14. The composition of claim 10, wherein the sweetness modifier is a flavoring with modifying properties selected from the group consisting of stevioside, steviolbioside rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, dulcoside B, rubusoside, alpha-glucosyl Stevia, fructosyl Stevia, galactosyl Stevia, beta-glucosyl Stevia, siamenoside, mogrosidc IV, mogroside V, Luo Han Guo, monatin, glycyrrhizic acid, thaumatin, a salt thereof, a glycosylated derivative thereof and a combination thereof.
15. The composition of claim 10, wherein the olfactory effective amount is from about 1 ppb to about 1000 ppm.
16. The composition of claim 10, wherein the olfactory effective amount is from about 5 ppb to about 100 ppm.
17. The composition of claim 10, wherein the olfactory effective amount is from about 10 ppb to about 10 ppm.
18. The composition of claim 10, wherein ligustrosidic acid or a derivative thereof is provided as a Carica papaya leave extract.
19. A consumable comprising a sweetness modifier and an olfactory effective amount of ligustrosidic acid or a derivative thereof.
20. The consumable of claim 19, wherein the consumable is a food product and ligustrosidic acid or a derivative thereof is provided as a Carica papaya leave extract.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024026225A1 (en) 2022-07-26 2024-02-01 International Flavors & Fragrances Inc. Robust flavor emulsions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024007104A1 (en) * 2022-07-04 2024-01-11 国际香料和香精公司 Novel glucopyranoside composition for enhancing sweetness

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2260326C2 (en) * 2003-07-08 2005-09-20 Научно-исследовательский институт пищеконцентратной промышленности и специальной пищевой технологии (Государственное научное учреждение) Method for obtaining jelly marmalade
JP2008505887A (en) * 2004-07-06 2008-02-28 幾夫 森本 A composition for preventing, treating or ameliorating cancer comprising papaya extract
US20070178123A1 (en) * 2006-01-27 2007-08-02 Deborah Levenson Flavor-enhancing compositions, method of manufacture, and methods of use
US20080014331A1 (en) * 2006-07-17 2008-01-17 Constantin Badalov Super sweet sugar crystals and syrups for health and method
CN101784201A (en) * 2007-06-08 2010-07-21 奇华顿股份有限公司 consumables
US8449936B2 (en) * 2008-02-25 2013-05-28 Givaudan Sa Flavor molecules
AU2010343073A1 (en) * 2009-12-28 2012-08-02 The Coca-Cola Company Sweetness enhancers, compositions thereof, and methods for use
US20110206786A1 (en) * 2010-02-23 2011-08-25 Brett Justin West Acai and Iridoid Based Formulations
MX369176B (en) * 2012-06-04 2019-10-23 Univ Autonoma Del Estado De Hidalgo Star Phytochemical compositions that can be used as disinfectants and preservatives for food.
CN103653238B (en) * 2012-09-17 2015-12-02 福建中烟工业有限责任公司 The application of papaya leaf extract in cigarette
KR101293687B1 (en) * 2012-12-20 2013-08-06 한아름영농조합법인 Papaya leaf tea, functional tea drink comprising the extract, and preparation method thereof
JP2015038043A (en) * 2013-08-19 2015-02-26 幾夫 森本 Composition for immunity activation
JP6315767B2 (en) * 2013-12-10 2018-04-25 長谷川香料株式会社 Taste improving agent for fruit flavored foods and drinks
KR20170032589A (en) * 2015-09-15 2017-03-23 하상섭 A process for preparing beverage of papaw
US11357246B2 (en) * 2015-10-29 2022-06-14 Firmenich Incorporated High intensity sweeteners
EP3246000A1 (en) * 2016-05-18 2017-11-22 Capsugel Belgium NV Separable capsule for sprinkling applications
WO2020014610A1 (en) * 2018-07-12 2020-01-16 International Flavors & Fragrances Inc. Verbascoside and related compounds for sweetness enhancement

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
Chen et al., "Determination of mannitol and three sugars in Ligustrum lucidum Ait. By capillary electrophoresis with electrochemical detection", Analytica Chemica Acta, 530, (2005), pp. 15-21. (Year: 2005) *
Kwon et al. - KR 101293687- Translated Abstract (Year: 2013) *
Lan, Z- CN 1931243 Translated Abstract. (Year: 2006) *
Li et al., "Application of UHPLC-ESI_Q-TOF-MS to Identify Multiple Constituents in Processed Products of the Herbal Medicine Ligustri Lucidi Fructus", Molecules, 22, 689, (2017), pp. 1-14. (Year: 2017) *
Richardson ,"How Sweet is Your Tea", Tea Time, September 17, 2014, https://teatimemagazine.com/sweet-tea/, downloaded December 2, 2023. (Year: 2014) *
Severson, K., "Showdown at the Coffee Shop", The New York Times, April 14, 2009, https://www.nytimes.com/2009/04/15/dining/15sweet.html, downloaded December 2, 2023. (Year: 2009) *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024026225A1 (en) 2022-07-26 2024-02-01 International Flavors & Fragrances Inc. Robust flavor emulsions

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